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Like Markovnikov, Saytzeff states his rule in terms, not of product stability, but of numbers of hydrogens on carbon atoms, (a) Suggest a wording for this original Saytzeff rule, (b) Predict the major product of dehydrohalogenation of 2-bromo-1-phenylbutane on the basis of the original rule, (c) On the basis of the modern rule.

An alternative mechanism for \(E_{2}\) elimination is the following: (a) Would this mechanism lead to a first-order kinetics with respect to the concentrations of \(\mathrm{OH}\) and ethy1 chloride? Explain. (b) This mechanism has been excluded for several halides by carrying out the reaction in deuterated solvents such as \(\mathrm{D}_{2} \mathrm{O}\) and \(\mathrm{C}_{2} \mathrm{H}_{5} \mathrm{OD}\). Explain how such experiments could be relevant to the reaction mechanism.

The reaction of \((\pm)-2,3\) -dibromobutane with ethoxide ion produces trans-2-bromo-2-butene while, under the same conditions, meso-2, 3 -dibromobutane produces the corresponding cis isomer. With the aid of three- dimensional representations, determine whether this is an anti (trans) elimination. Explain how it is possible for a "trans" elimination to produce both cis and trans product.

Predict the order of reactivity of the following halides with (a) sodium iodide in acetone; (b) aqueous alcoholic silver nitrate.

Predict the order of reactivity of the following halides with (a) sodium iodide in acetone; (b) aqueous alcoholic silver nitrate:

The reaction of t-buty1 chloride with water is strongly accelerated by sodium hydroxide. How would the ratio of elimination to substitution products be effected thereby?